SML0772
Curvularin
from Penicillium citrinum, ≥98% (HPLC)
Synonym(s):
2H-3-Benzoxacyclododecin-2,10(1H)-dione, 4,5,6,7,8,9-hexahydro-11,13-dihydroxy-4-methyl-,(4S)-
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About This Item
Empirical Formula (Hill Notation):
C16H20O5
CAS Number:
Molecular Weight:
292.33
MDL number:
UNSPSC Code:
51111800
PubChem Substance ID:
NACRES:
NA.77
Recommended Products
biological source
Penicillium citrinum
Quality Level
Assay
≥98% (HPLC)
form
powder
solubility
DMSO: 1 mg/mL
storage temp.
−20°C
SMILES string
OC1=C(C(CCCCC[C@H](C)O2)=O)C(CC2=O)=CC(O)=C1
InChI
1S/C16H20O5/c1-10-5-3-2-4-6-13(18)16-11(8-15(20)21-10)7-12(17)9-14(16)19/h7,9-10,17,19H,2-6,8H2,1H3/t10-/m0/s1
InChI key
VDUIGYAPSXCJFC-JTQLQIEISA-N
Biochem/physiol Actions
S - Curvularin is a macrocyclic lactone with cytotoxic activity. Curvularin inhibits cell division as well as expression of human inducible nitric oxide synthase (iNOS), an enzyme critically involved in pro-inflammatory immune processes. Curvularin anti-inflammatory activity was demonstrated in chronic inflammatory disease models in mice such as Chronic Induced Arthritis (CIA) as well as in human alveolar epithelial A549/8 cells.
Reconstitution
Soluble in DMSO (1 mg/mL), Chloroform (3 mg/mL) and Dichloromethane (3 mg/mL). Note: Insoluble in water.
Other Notes
Store the product sealed at −20 °C. Under these conditions the product is stable for at least 5 years.
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Birgitte Andersen et al.
International journal of food microbiology, 126(1-2), 172-179 (2008-07-05)
Ulocladium, which is phylogenetically related to Alternaria, contains species that are food spoilers and plant pathogens, but also species that have potential as enzyme producers and bio-control agents. Ulocladium spp. are often found on dead vegetation, in soil, air and
Lian Wu Xie et al.
Applied biochemistry and biotechnology, 159(1), 284-293 (2009-04-01)
With the anti-microbial and anti-tumor composite screening model, bioassay-guided fractionation led to the isolation of two structurally related bioactive compounds, curvularin and alphabeta-dehydrocurvularin, from ethyl acetate extract of Eupenicillium sp. associated with marine sponge Axinella sp. Further study on the
Kristina Rudolph et al.
Cytokine, 61(1), 285-296 (2012-11-09)
TGF-β is a multifunctional cytokine that regulates cell proliferation, differentiation, apoptosis and extracellular matrix production. Deregulation of TGF-β production or signaling plays a pivotal role in a variety of pathological processes such as cancer, metastasis, angiogenesis and fibrosis. Therefore, TGF-β
Jixun Zhan et al.
Journal of natural products, 68(8), 1271-1273 (2005-08-30)
The microbiological transformation of curvularin (1) with Beauveria bassiana ATCC 7159 afforded three new metabolites identified as curvularin-7-O-beta-D-glucopyranoside (2), curvularin-4'-O-methyl-7-O-beta-D-glucopyranoside (3), and 6-hydroxycurvularin-4'-O-methyl-6-O-beta-D-glucopyranoside (4) resulting from hydroxylation, glucosidation, and methylglucosidation of the substrate. Isolation of 6-methyl-2,4-dihydroxyphenyl-4'-O-methyl-1-O-beta-D-glucopyranoside (5) from the fermentation
Pamela M Tadross et al.
Organic letters, 12(7), 1612-1614 (2010-03-04)
A general approach for the synthesis of benzannulated macrolactone natural products utilizing an aryne acyl-alkylation reaction is described. Toward this end, the total syntheses of the natural products (-)-curvularin, curvulin, and (-)-diplodialide C are reported. Furthermore, the aryne insertion technology
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